4-{1-[4-(4-Bromo-phen-yl)-1,3-thia-zol-2-yl]-5-(4-fluoro-phen-yl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazole.

In the title compound, C(28)H(22)BrFN(6)S, the central pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angles between the least-squares plane through this ring and the adjacent thia-zole [18.81 (15)°] and triazole [1.83 (16)°] rings indicate a twist in the mol-ecule. A further twist is evident by the dihedral angle of 64.48 (16)° between the triazole ring and the attached benzene ring. In the crystal, C-H⋯N, C-H⋯F, C-H⋯π and π-π inter-actions [occurring between the thia-zole and triazole rings, centroid-centroid distance = 3.571 (2) Å] link mol-ecules into a three-dimensional architecture. The sample studied was a non-merohedral twin; the minor twin component refined to 47.16 (7)%.

Related literature

For the biological activity of related compounds, see: Abdel-Wahab et al. (2009 ▶, 2012a ▶). For a related pyrazolyl-1,2,3-triazole structure, see: Abdel-Wahab et al. (2012b ▶). For the deconvolution of twinned data, see: Spek (2009 ▶).

Experimental

Crystal data

C28H22BrFN6S

M = 573.49

Orthorhombic,

a = 11.3476 (7) Å

b = 14.0549 (8) Å

c = 15.954 (7) Å

V = 2544.5 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.74 mm−1

T = 100 K

0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.695, T max = 1.000

7265 measured reflections

5293 independent reflections

4819 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.077

S = 1.02

5293 reflections

336 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.50 e Å−3

Absolute structure: Flack (1983 ▶), 2028 Friedel pairs

Flack parameter: 0.001 (7)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024257/su2440sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024257/su2440Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024257/su2440Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H22BrFN6S	F(000) = 1168
Mr = 573.49	Dx = 1.497 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3622 reflections
a = 11.3476 (7) Å	θ = 2.6–27.5°
b = 14.0549 (8) Å	µ = 1.74 mm−1
c = 15.954 (7) Å	T = 100 K
V = 2544.5 (12) Å3	Prism, light-brown
Z = 4	0.40 × 0.20 × 0.10 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	5293 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4819 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −14→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −17→12
Tmin = 0.695, Tmax = 1.000	l = −20→11
7265 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0325P)2 + 0.2812P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5293 reflections	Δρmax = 0.36 e Å−3
336 parameters	Δρmin = −0.50 e Å−3
0 restraints	Absolute structure: Flack (1983), 2028 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.001 (7)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.23440 (3)	0.94410 (2)	−0.361341 (19)	0.02124 (8)
S1	0.66530 (6)	0.86176 (5)	0.08004 (5)	0.01822 (17)
F1	0.94395 (17)	1.26252 (12)	−0.25372 (13)	0.0294 (5)
N1	1.2170 (2)	0.77775 (16)	0.21438 (15)	0.0152 (5)
N2	1.2929 (2)	0.78394 (16)	0.14807 (16)	0.0174 (5)
N3	1.2310 (2)	0.81441 (16)	0.08489 (15)	0.0154 (5)
N4	0.9210 (2)	0.87452 (17)	0.06940 (16)	0.0171 (5)
N5	0.8648 (2)	0.91513 (18)	0.00017 (16)	0.0170 (5)
N6	0.6859 (2)	0.91897 (16)	−0.07364 (16)	0.0155 (5)
C1	1.2602 (3)	0.7492 (2)	0.29537 (18)	0.0167 (6)
C2	1.2594 (3)	0.8146 (2)	0.36070 (19)	0.0208 (6)
H2	1.2265	0.8761	0.3532	0.025*
C3	1.3073 (3)	0.7883 (2)	0.4366 (2)	0.0255 (7)
H3	1.3062	0.8322	0.4818	0.031*
C4	1.3573 (3)	0.6990 (2)	0.4485 (2)	0.0247 (7)
C5	1.3549 (3)	0.6346 (2)	0.3825 (2)	0.0247 (8)
H5	1.3869	0.5728	0.3902	0.030*
C6	1.3067 (3)	0.6589 (2)	0.3059 (2)	0.0204 (7)
H6	1.3055	0.6144	0.2611	0.024*
C7	1.4158 (3)	0.6738 (3)	0.5301 (2)	0.0366 (9)
H7A	1.3946	0.6086	0.5458	0.055*
H7B	1.3895	0.7179	0.5739	0.055*
H7C	1.5016	0.6785	0.5238	0.055*
C8	1.0046 (3)	0.8013 (2)	0.2515 (2)	0.0178 (6)
H8A	1.0048	0.7410	0.2823	0.027*
H8B	0.9310	0.8072	0.2199	0.027*
H8C	1.0112	0.8543	0.2912	0.027*
C9	1.1057 (3)	0.8035 (2)	0.1929 (2)	0.0151 (6)
C10	1.1170 (3)	0.8273 (2)	0.10935 (19)	0.0142 (6)
C11	1.0306 (3)	0.8628 (2)	0.05071 (18)	0.0138 (6)
C12	1.0619 (3)	0.8935 (2)	−0.03664 (19)	0.0170 (6)
H12A	1.1013	0.8416	−0.0678	0.020*
H12B	1.1138	0.9501	−0.0361	0.020*
C13	0.9411 (2)	0.9169 (2)	−0.07472 (19)	0.0148 (6)
H13	0.9171	0.8647	−0.1138	0.018*
C14	0.9378 (2)	1.0115 (2)	−0.12096 (18)	0.0159 (6)
C15	0.8894 (3)	1.0932 (2)	−0.0868 (2)	0.0196 (7)
H15	0.8547	1.0910	−0.0326	0.024*
C16	0.8913 (3)	1.1791 (2)	−0.1314 (2)	0.0241 (7)
H16	0.8576	1.2353	−0.1085	0.029*
C17	0.9427 (3)	1.1797 (2)	−0.2088 (2)	0.0208 (7)
C18	0.9940 (3)	1.1004 (2)	−0.2437 (2)	0.0188 (7)
H18	1.0310	1.1036	−0.2971	0.023*
C19	0.9906 (3)	1.0161 (2)	−0.1994 (2)	0.0177 (6)
H19	1.0247	0.9604	−0.2229	0.021*
C20	0.7446 (3)	0.90135 (18)	−0.00607 (17)	0.0152 (6)
C21	0.5397 (3)	0.8702 (2)	0.0193 (2)	0.0190 (7)
H21	0.4623	0.8560	0.0382	0.023*
C22	0.5671 (3)	0.8999 (2)	−0.0593 (2)	0.0171 (7)
C23	0.4858 (2)	0.91170 (19)	−0.1308 (2)	0.0155 (6)
C24	0.5272 (2)	0.9486 (2)	−0.20621 (19)	0.0180 (6)
H24	0.6073	0.9676	−0.2105	0.022*
C25	0.4538 (3)	0.9581 (2)	−0.27493 (19)	0.0197 (7)
H25	0.4831	0.9831	−0.3262	0.024*
C26	0.3367 (3)	0.9305 (2)	−0.26774 (19)	0.0168 (6)
C27	0.2930 (3)	0.8929 (2)	−0.1943 (2)	0.0204 (7)
H27	0.2129	0.8736	−0.1906	0.025*
C28	0.3677 (3)	0.8836 (2)	−0.1253 (2)	0.0197 (7)
H28	0.3383	0.8581	−0.0743	0.024*

	U11	U22	U33	U12	U13	U23
Br1	0.02349 (14)	0.02282 (14)	0.01741 (15)	−0.00056 (13)	−0.00417 (13)	0.00095 (13)
S1	0.0157 (3)	0.0244 (4)	0.0145 (4)	−0.0021 (3)	0.0021 (3)	0.0024 (3)
F1	0.0288 (10)	0.0224 (9)	0.0372 (12)	−0.0012 (9)	−0.0056 (10)	0.0159 (9)
N1	0.0152 (12)	0.0186 (11)	0.0117 (13)	−0.0003 (10)	−0.0012 (10)	−0.0026 (10)
N2	0.0187 (12)	0.0181 (11)	0.0153 (14)	0.0005 (10)	0.0004 (11)	−0.0009 (11)
N3	0.0176 (12)	0.0168 (11)	0.0119 (12)	0.0000 (11)	−0.0006 (11)	0.0005 (10)
N4	0.0181 (12)	0.0197 (12)	0.0137 (14)	0.0004 (11)	−0.0021 (11)	0.0045 (11)
N5	0.0126 (11)	0.0257 (13)	0.0128 (13)	−0.0008 (10)	0.0031 (10)	0.0055 (11)
N6	0.0126 (11)	0.0174 (12)	0.0166 (13)	0.0018 (10)	0.0022 (10)	0.0014 (10)
C1	0.0150 (13)	0.0222 (13)	0.0130 (14)	−0.0009 (13)	−0.0013 (13)	0.0050 (11)
C2	0.0214 (14)	0.0231 (13)	0.0178 (15)	0.0020 (12)	−0.0002 (16)	−0.0005 (13)
C3	0.0273 (17)	0.0338 (18)	0.0153 (17)	−0.0043 (15)	−0.0011 (14)	−0.0030 (14)
C4	0.0226 (16)	0.0355 (18)	0.0161 (17)	−0.0044 (15)	−0.0018 (13)	0.0095 (15)
C5	0.0236 (15)	0.0221 (15)	0.028 (2)	0.0002 (14)	−0.0025 (14)	0.0073 (14)
C6	0.0188 (14)	0.0219 (15)	0.0204 (17)	−0.0012 (13)	−0.0020 (13)	−0.0002 (13)
C7	0.033 (2)	0.057 (2)	0.020 (2)	−0.0065 (19)	−0.0102 (17)	0.0115 (18)
C8	0.0159 (13)	0.0236 (15)	0.0139 (15)	0.0004 (12)	0.0026 (12)	0.0021 (13)
C9	0.0143 (14)	0.0143 (14)	0.0166 (16)	−0.0011 (12)	0.0012 (12)	−0.0013 (12)
C10	0.0175 (13)	0.0129 (13)	0.0123 (15)	−0.0016 (12)	0.0007 (12)	0.0018 (11)
C11	0.0160 (13)	0.0145 (13)	0.0109 (15)	−0.0034 (12)	0.0020 (12)	−0.0032 (12)
C12	0.0147 (14)	0.0203 (15)	0.0161 (16)	0.0012 (12)	0.0024 (13)	0.0046 (13)
C13	0.0146 (13)	0.0171 (14)	0.0128 (15)	−0.0004 (12)	0.0007 (12)	0.0010 (12)
C14	0.0116 (13)	0.0197 (14)	0.0165 (17)	−0.0018 (12)	−0.0034 (12)	0.0045 (12)
C15	0.0190 (14)	0.0231 (15)	0.0167 (17)	0.0005 (13)	0.0012 (13)	0.0015 (13)
C16	0.0200 (14)	0.0212 (15)	0.031 (2)	0.0050 (12)	−0.0010 (16)	−0.0028 (16)
C17	0.0183 (15)	0.0195 (15)	0.0244 (18)	−0.0034 (13)	−0.0075 (14)	0.0130 (14)
C18	0.0135 (14)	0.0278 (16)	0.0152 (16)	−0.0032 (13)	−0.0026 (13)	0.0070 (14)
C19	0.0140 (14)	0.0199 (14)	0.0191 (17)	0.0012 (12)	−0.0035 (13)	−0.0010 (13)
C20	0.0152 (14)	0.0159 (12)	0.0146 (14)	0.0030 (12)	0.0020 (12)	0.0017 (11)
C21	0.0154 (14)	0.0218 (15)	0.0198 (17)	−0.0011 (13)	0.0004 (13)	0.0017 (14)
C22	0.0163 (14)	0.0161 (14)	0.0190 (17)	0.0017 (12)	−0.0014 (13)	−0.0002 (13)
C23	0.0152 (13)	0.0138 (12)	0.0175 (16)	0.0025 (11)	0.0003 (13)	0.0018 (13)
C24	0.0150 (13)	0.0164 (14)	0.0226 (16)	−0.0011 (13)	0.0009 (12)	0.0011 (14)
C25	0.0217 (14)	0.0193 (15)	0.0180 (16)	0.0031 (13)	0.0014 (13)	0.0037 (13)
C26	0.0184 (14)	0.0163 (14)	0.0158 (15)	0.0043 (13)	−0.0044 (12)	−0.0001 (12)
C27	0.0145 (15)	0.0253 (16)	0.0215 (17)	−0.0012 (12)	0.0009 (13)	−0.0001 (13)
C28	0.0185 (14)	0.0243 (15)	0.0161 (18)	0.0005 (12)	0.0029 (13)	0.0016 (13)

Br1—C26	1.901 (3)	C8—H8C	0.9800
S1—C21	1.728 (3)	C9—C10	1.381 (4)
S1—C20	1.734 (3)	C10—C11	1.445 (4)
F1—C17	1.367 (3)	C11—C12	1.501 (4)
N1—C9	1.358 (4)	C12—C13	1.535 (4)
N1—N2	1.367 (3)	C12—H12A	0.9900
N1—C1	1.439 (4)	C12—H12B	0.9900
N2—N3	1.300 (3)	C13—C14	1.521 (4)
N3—C10	1.363 (4)	C13—H13	1.0000
N4—C11	1.290 (4)	C14—C19	1.389 (4)
N4—N5	1.397 (3)	C14—C15	1.385 (4)
N5—C20	1.381 (4)	C15—C16	1.402 (4)
N5—C13	1.475 (4)	C15—H15	0.9500
N6—C20	1.291 (4)	C16—C17	1.365 (5)
N6—C22	1.394 (4)	C16—H16	0.9500
C1—C6	1.384 (4)	C17—C18	1.376 (4)
C1—C2	1.390 (4)	C18—C19	1.380 (4)
C2—C3	1.377 (4)	C18—H18	0.9500
C2—H2	0.9500	C19—H19	0.9500
C3—C4	1.390 (5)	C21—C22	1.357 (4)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.388 (5)	C22—C23	1.476 (4)
C4—C7	1.504 (4)	C23—C24	1.392 (4)
C5—C6	1.383 (4)	C23—C28	1.400 (4)
C5—H5	0.9500	C24—C25	1.383 (4)
C6—H6	0.9500	C24—H24	0.9500
C7—H7A	0.9800	C25—C26	1.390 (4)
C7—H7B	0.9800	C25—H25	0.9500
C7—H7C	0.9800	C26—C27	1.378 (4)
C8—C9	1.480 (4)	C27—C28	1.396 (4)
C8—H8A	0.9800	C27—H27	0.9500
C8—H8B	0.9800	C28—H28	0.9500
C21—S1—C20	87.81 (15)	C13—C12—H12B	111.3
C9—N1—N2	112.0 (2)	H12A—C12—H12B	109.2
C9—N1—C1	128.1 (3)	N5—C13—C14	113.2 (2)
N2—N1—C1	119.9 (2)	N5—C13—C12	101.5 (2)
N3—N2—N1	106.3 (2)	C14—C13—C12	113.6 (2)
N2—N3—C10	109.5 (2)	N5—C13—H13	109.4
C11—N4—N5	108.0 (2)	C14—C13—H13	109.4
C20—N5—N4	116.8 (2)	C12—C13—H13	109.4
C20—N5—C13	121.5 (3)	C19—C14—C15	119.2 (3)
N4—N5—C13	112.3 (2)	C19—C14—C13	117.9 (3)
C20—N6—C22	109.0 (2)	C15—C14—C13	122.9 (3)
C6—C1—C2	121.2 (3)	C14—C15—C16	120.5 (3)
C6—C1—N1	119.6 (3)	C14—C15—H15	119.7
C2—C1—N1	119.1 (3)	C16—C15—H15	119.7
C3—C2—C1	118.6 (3)	C17—C16—C15	118.1 (3)
C3—C2—H2	120.7	C17—C16—H16	120.9
C1—C2—H2	120.7	C15—C16—H16	120.9
C2—C3—C4	121.6 (3)	C16—C17—F1	119.0 (3)
C2—C3—H3	119.2	C16—C17—C18	122.8 (3)
C4—C3—H3	119.2	F1—C17—C18	118.2 (3)
C3—C4—C5	118.5 (3)	C17—C18—C19	118.4 (3)
C3—C4—C7	120.8 (3)	C17—C18—H18	120.8
C5—C4—C7	120.8 (3)	C19—C18—H18	120.8
C6—C5—C4	121.2 (3)	C14—C19—C18	120.9 (3)
C6—C5—H5	119.4	C14—C19—H19	119.6
C4—C5—H5	119.4	C18—C19—H19	119.6
C5—C6—C1	119.0 (3)	N6—C20—N5	122.9 (3)
C5—C6—H6	120.5	N6—C20—S1	117.1 (2)
C1—C6—H6	120.5	N5—C20—S1	120.0 (2)
C4—C7—H7A	109.5	C22—C21—S1	110.5 (2)
C4—C7—H7B	109.5	C22—C21—H21	124.7
H7A—C7—H7B	109.5	S1—C21—H21	124.7
C4—C7—H7C	109.5	C21—C22—N6	115.6 (3)
H7A—C7—H7C	109.5	C21—C22—C23	127.2 (3)
H7B—C7—H7C	109.5	N6—C22—C23	117.1 (3)
C9—C8—H8A	109.5	C24—C23—C28	118.9 (3)
C9—C8—H8B	109.5	C24—C23—C22	119.9 (3)
H8A—C8—H8B	109.5	C28—C23—C22	121.2 (3)
C9—C8—H8C	109.5	C25—C24—C23	121.2 (3)
H8A—C8—H8C	109.5	C25—C24—H24	119.4
H8B—C8—H8C	109.5	C23—C24—H24	119.4
N1—C9—C10	102.8 (3)	C24—C25—C26	118.9 (3)
N1—C9—C8	123.8 (3)	C24—C25—H25	120.6
C10—C9—C8	133.4 (3)	C26—C25—H25	120.6
N3—C10—C9	109.4 (3)	C27—C26—C25	121.4 (3)
N3—C10—C11	120.3 (3)	C27—C26—Br1	119.2 (2)
C9—C10—C11	130.2 (3)	C25—C26—Br1	119.4 (2)
N4—C11—C10	123.3 (3)	C26—C27—C28	119.2 (3)
N4—C11—C12	114.0 (3)	C26—C27—H27	120.4
C10—C11—C12	122.7 (3)	C28—C27—H27	120.4
C11—C12—C13	102.6 (2)	C27—C28—C23	120.4 (3)
C11—C12—H12A	111.3	C27—C28—H28	119.8
C13—C12—H12A	111.3	C23—C28—H28	119.8
C11—C12—H12B	111.3
C9—N1—N2—N3	0.7 (3)	C11—C12—C13—C14	132.8 (3)
C1—N1—N2—N3	−177.6 (2)	N5—C13—C14—C19	−169.6 (3)
N1—N2—N3—C10	−0.4 (3)	C12—C13—C14—C19	75.3 (3)
C11—N4—N5—C20	156.5 (3)	N5—C13—C14—C15	13.2 (4)
C11—N4—N5—C13	9.4 (3)	C12—C13—C14—C15	−101.9 (3)
C9—N1—C1—C6	118.3 (3)	C19—C14—C15—C16	1.3 (4)
N2—N1—C1—C6	−63.7 (4)	C13—C14—C15—C16	178.5 (3)
C9—N1—C1—C2	−64.7 (4)	C14—C15—C16—C17	−0.5 (5)
N2—N1—C1—C2	113.3 (3)	C15—C16—C17—F1	179.1 (3)
C6—C1—C2—C3	0.7 (5)	C15—C16—C17—C18	−1.0 (5)
N1—C1—C2—C3	−176.2 (3)	C16—C17—C18—C19	1.7 (5)
C1—C2—C3—C4	0.9 (5)	F1—C17—C18—C19	−178.5 (3)
C2—C3—C4—C5	−2.0 (5)	C15—C14—C19—C18	−0.7 (4)
C2—C3—C4—C7	176.2 (3)	C13—C14—C19—C18	−178.0 (3)
C3—C4—C5—C6	1.6 (5)	C17—C18—C19—C14	−0.8 (4)
C7—C4—C5—C6	−176.6 (3)	C22—N6—C20—N5	−178.7 (3)
C4—C5—C6—C1	0.0 (5)	C22—N6—C20—S1	−0.4 (3)
C2—C1—C6—C5	−1.2 (5)	N4—N5—C20—N6	−166.6 (3)
N1—C1—C6—C5	175.8 (3)	C13—N5—C20—N6	−22.6 (4)
N2—N1—C9—C10	−0.7 (3)	N4—N5—C20—S1	15.2 (4)
C1—N1—C9—C10	177.5 (3)	C13—N5—C20—S1	159.2 (2)
N2—N1—C9—C8	178.3 (3)	C21—S1—C20—N6	−0.3 (2)
C1—N1—C9—C8	−3.5 (5)	C21—S1—C20—N5	178.0 (2)
N2—N3—C10—C9	−0.1 (3)	C20—S1—C21—C22	1.0 (2)
N2—N3—C10—C11	178.7 (2)	S1—C21—C22—N6	−1.5 (3)
N1—C9—C10—N3	0.5 (3)	S1—C21—C22—C23	176.9 (2)
C8—C9—C10—N3	−178.4 (3)	C20—N6—C22—C21	1.2 (4)
N1—C9—C10—C11	−178.2 (3)	C20—N6—C22—C23	−177.4 (2)
C8—C9—C10—C11	2.9 (6)	C21—C22—C23—C24	176.1 (3)
N5—N4—C11—C10	176.4 (3)	N6—C22—C23—C24	−5.6 (4)
N5—N4—C11—C12	−1.1 (3)	C21—C22—C23—C28	−6.0 (5)
N3—C10—C11—N4	178.4 (3)	N6—C22—C23—C28	172.4 (3)
C9—C10—C11—N4	−3.1 (5)	C28—C23—C24—C25	0.3 (4)
N3—C10—C11—C12	−4.3 (4)	C22—C23—C24—C25	178.3 (3)
C9—C10—C11—C12	174.2 (3)	C23—C24—C25—C26	0.3 (5)
N4—C11—C12—C13	−6.8 (3)	C24—C25—C26—C27	−0.8 (5)
C10—C11—C12—C13	175.6 (2)	C24—C25—C26—Br1	179.5 (2)
C20—N5—C13—C14	79.6 (3)	C25—C26—C27—C28	0.8 (4)
N4—N5—C13—C14	−135.1 (2)	Br1—C26—C27—C28	−179.5 (2)
C20—N5—C13—C12	−158.3 (3)	C26—C27—C28—C23	−0.3 (4)
N4—N5—C13—C12	−12.9 (3)	C24—C23—C28—C27	−0.3 (4)
C11—C12—C13—N5	11.0 (3)	C22—C23—C28—C27	−178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2i	1.00	2.58	3.488 (4)	151
C27—H27···F1ii	0.95	2.53	3.358 (4)	146
C8—H8A···Cg1iii	0.98	2.84	3.401 (3)	117

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C23–C28 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2i	1.00	2.58	3.488 (4)	151
C27—H27⋯F1ii	0.95	2.53	3.358 (4)	146
C8—H8A⋯Cg1iii	0.98	2.84	3.401 (3)	117

Symmetry codes: (i) ; (ii) ; (iii) .